Total syntheses of various members of the ergot family are being pursued through the use of intramolecular (3 plus 2) dipolar cycloaddition reactions of nitrile oxides. Lysergic acid, paliclavine and fumigaclavine B are the products now under consideration. The new compounds produced during these studies will be available for screening as potential prolactin inhibitors, antitumor and cardiovascular agents. The synthesis of a related indole alkaloid, clavicipictic acid, is also being investigated. Our projected scheme is patterned after the proposed biosynthetic pathway to this unique natural product.